The kids over at the rpg site are discussing whether or not the collective output of the "OSR" has been better, or could be better, than that of TSR.
My own feeling is that, whatever the answer, the OSR certainly creates better dungeoneering materials than TSR did, but the opposite side of that coin is that The Dungeon, and particularly The Megadungeon, are fetishized within the OSR to a far greater degree than they ever were during the TSR era. This is especially true of the 2nd edition period, when many of the major campaign setting materials created - Al Qadim, Dark Sun, Planescape, Spelljammer, and so on - specifically and deliberately eschewed The Dungeon as the locus of play.
The obsession with The Dungeon is a source of some mystery to me, as somebody too young to have played 1st edition. Although, equally, it's clear that it comes from a preference for that play style among the early OSR heavyweights, and that this has, in turn, influenced the development of the movement (such as it is). I like dungeons, but it's far from my favourite method of play, which would revolve around city-based and/or wilderness exploration. What excites me most is not the insular dungeon layout, but an open hex map full of interesting areas to explore and range over, and interesting locales to interact with.
In that area it's very hard to say that the OSR has produced much good at all. I could be wrong, but the only products that spring to mind in that regard are Carcosa and Isle of the Unknown, both of which I find pretty uninspired, and the Sin Nomine and Land of Nod stuff - which is good, but nowhere near extensive enough to say that it is in any way challenging of the grand TSR setting creation machine that was at work in the 1990s.